Ross,
I'm the developer of STACK. STACK is used by a large and growing number of institutions with very large groups of students, mostly through Moodle. There is an ILIAS interface, and we use it in Edinburgh via the LTI interface.
The authoring "quick start" guide is here: https://stack.maths.ed.ac.uk/demo/question/type/stack/doc/doc.php/Authoring/Authoring_quick_start.md
I can give you (or anyone else with a ".ac.uk" or other sensible credentials) teacher access to a demo course if this helps. STACK is a sophisticated tool.
WebWork certainly has the edge over STACK when it comes to question banks and problem libraries, but I've not compromised on the mathematics. My goal was also to create something teachers can author for themselves, but I think the process is fundamentally complex problem.
If you'd like to know more let me know.
Chris
--
The University of Edinburgh is a charitable body, registered in
Scotland, with registration number SC005336.
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